Call us at (475) 244-9781 to learn more about active adult communities in Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
125 communities near Cheshire
298 homes near Cheshire
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![Castle Heights of Cheshir...]()
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
3 rating (2 reviews)
![Heritage Hills]()
$400Ks
- $700Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1975 - 2003
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $500Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
No reviews yet
![The Greens at Half Hollow]()
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
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(475) 244-9781
No reviews yet
![Rivington]()
$400Ks
- $1Ms
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$300Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$400Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Meadowbrook Pointe Athlet...]()
$800Ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$900Ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (1 reviews)
![Fairfield at St. James]()
$500Ks
- $600Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
No reviews yet
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $300Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
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Questions? Call us:
(475) 244-9781
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
No reviews yet
![The Seasons at East Meado...]()
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![Dutchgate]()
$400Ks
- $400Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet
![The Waterways at Moriches]()
$500Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$300Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$600Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
4 rating (1 reviews)
![Vineyards at Blue Point]()
$600Ks
- $900Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
No reviews yet
![HarborView]()
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
No reviews yet
![The Seasons at Elwood]()
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$700Ks
- $800Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$600Ks
- $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
No reviews yet
![Woodridge Strathmore Terr...]()
$300Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
No reviews yet
![Country Village Estates]()
$400Ks
- $400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $400Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
Greenwood Village
![48 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|960 sq ft
|Condo
48 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 821669 • Brookhampton Realty, Kevin N. Loiaco...
Leisure Village
![320 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,486 sq ft
|Condo
320 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 817991 • Coldwell Banker M&D Good Life, Micha...
Glenwood Village
![1661 OLD COUNTRY RD UNIT 521, RIVERHEAD,..., Riverhead, NY 11901]()
MLS L3593702 • Moriches Bay Realty, Geraldine S. ...
Leisure Knoll
![2 LAMONT RD # 2, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS L3568605 • Coldwell Banker American Homes, Ka...
The Gardens of Wilbraham
![45 IVY CIR # 45, WILBRAHAM, MA, 01095, Wilbraham, MA 01095]()
2 beds
|3 baths
|1,752 sq ft
|Condo
45 IVY CIR # 45, WILBRAHAM, MA, 01095
Community: The Gardens of Wilbraham
MLS 73328184 • Coldwell Banker Realty - Western M...
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Questions? Call us:
(475) 244-9781
Glenwood Village
![1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,270 sq ft
|Mobile Home
1661 OLD COUNTRY RD 435, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 827152 • Douglas Elliman Real Estate, Allison...
Knickerbocker Bay Club
![433 MAIN ST 203, PORT WASHINGTON, NY, 11..., Port Washington, NY 11050]()
2 beds
|2 baths
|1,323 sq ft
|Condo
433 MAIN ST 203, PORT WASHINGTON, NY, 11...
Community: Knickerbocker Bay Club
MLS 865024 • Douglas Elliman Real Estate, Kristin...
Meadowbrook Pointe Links & Spa
![142 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|1,691 sq ft
|Condo
142 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 843695 • Signature Premier Properties, Matthe...
Meadowbrook Pointe Links & Spa
![42 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|1,534 sq ft
|Condo
42 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 841734 • Signature Premier Properties, Matthe...
Foxwood Village
![1407 MIDDLE RD 203, CALVERTON, NY, 11933, Calverton, NY 11933]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD 203, CALVERTON, NY, 11933
Community: Foxwood Village
MLS 866087 • Joanne Kane Gigantiello, Joanne Giga...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Country Pointe Plainview
![17101 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803]()
2 beds
|2 baths
|1,443 sq ft
|Condo
17101 ASPENWOOD DR, PLAINVIEW, NY, 11803
Community: Country Pointe Plainview
MLS 857869 • Douglas Elliman Real Estate, Ellen A...
Stone Ridge Estates
![156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,700 sq ft
|Condo
156 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 859377 • Howard Hanna Coach, Susan Catik
Leisure Glen
![437 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 860948 • RE/MAX Signature Real Estate, Julie ...
Founders Village
![2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971, Southold, NY 11971]()
2 beds
|2 baths
|1,100 sq ft
|Condo
2555 YOUNGS AVE 11D, SOUTHOLD, NY, 11971
Community: Founders Village
MLS 828475 • Signature Premier Properties, Patric...
Heritage Hills
![116 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,144 sq ft
|Condo
116 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 863774 • Houlihan Lawrence Inc., David J. Hov...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
The Bel Aire at East Meadow
![50 MERRICK AVE 313, EAST MEADOW, NY, 115..., East Meadow, NY 11554]()
2 beds
|2 baths
|1,000 sq ft
|Condo
50 MERRICK AVE 313, EAST MEADOW, NY, 115...
Community: The Bel Aire at East Meadow
MLS 865749 • BERKSHIRE HATHAWAY, Michael J. Fink ...
Leisure Knoll
![140A LAURANCE LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 857230 • Coldwell Banker American Homes, Mary...
Greenwood Village
![21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
21 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 866101 • Signature Premier Properties, Meliss...
The Waterways at Moriches
![381 QUARRY POND CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|2,200 sq ft
|Condo
381 QUARRY POND CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 865568 • Century 21 Cor Ace Realty Inc, James...
Fairfield at St. James
![314 ELTON CT N, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,246 sq ft
|Condo
314 ELTON CT N, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 865013 • Daniel Gale Sothebys Intl Rlty, Mari...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Country Village Estates
![192 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,308 sq ft
|Condo
192 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 865313 • Realty Connect USA L I Inc, Bonnie S...
Leisure Knoll
![561 STRATFORD LN # 561, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,150 sq ft
|Condo
561 STRATFORD LN # 561, RIDGE, NY, 11961
Community: Leisure Knoll
MLS 863767 • Leisure Living Realty Inc, Paulina R...
The Greens at Half Hollow
![657 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|3 baths
|1,941 sq ft
|Townhouse
657 BALFOUR PL, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 862904 • Signature Premier Properties, Janice...
Sunrise Village
![186 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
2 beds
|2 baths
|1,046 sq ft
|Condo
186 REVERE DR, SAYVILLE, NY, 11782
Community: Sunrise Village
MLS 861890 • Douglas Elliman Real Estate, Lisa F....
Leisure Knoll
![190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 863784 • Coldwell Banker American Homes, Bonn...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
HarborView
![100 HARBOR VIEW DR APT 515, PORT WASHING..., Port Washington, NY 11050]()
2 beds
|3 baths
|1,495 sq ft
|Condo
100 HARBOR VIEW DR APT 515, PORT WASHING...
Community: HarborView
MLS 864376 • Daniel Gale Sothebys Intl Rlty, Mary...
Greenwood Village
![12 ORANGE TREE, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,283 sq ft
|Condo
12 ORANGE TREE, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 855697 • Signature Premier Properties, Maryan...
Meadowbrooke Pointe East Meadow
![506 EMANUEL WAY # 73, EAST MEADOW, NY, 1..., East Meadow, NY 11554]()
1 beds
|2 baths
|961 sq ft
|Condo
506 EMANUEL WAY # 73, EAST MEADOW, NY, 1...
Community: Meadowbrooke Pointe East Meadow
MLS 863045 • Premier Prop At Meadowbrook Pt, Mark...
Meadowbrooke Pointe East Meadow
![514 EMANUEL WAY # 77, EAST MEADOW, NY, 1..., East Meadow, NY 11554]()
1 beds
|3 baths
|2,061 sq ft
|Condo
514 EMANUEL WAY # 77, EAST MEADOW, NY, 1...
Community: Meadowbrooke Pointe East Meadow
MLS 859169 • Premier Prop At Meadowbrook Pt, Mark...
Greenwood Village
![5112 VILLAGE CIR 5112, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,287 sq ft
|Condo
5112 VILLAGE CIR 5112, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS L3587229 • Gateway to The Hamptons R E, Vivia...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villas at Narragansett
![606 NARRAGANSETT VILLAS DR # 606, LINDEN..., Lindenhurst, NY 11757]()
2 beds
|2 baths
|1,215 sq ft
|Condo
606 NARRAGANSETT VILLAS DR # 606, LINDEN...
Community: The Villas at Narragansett
MLS 858116 • Hopes Quality Home Realty LLC, Linda...
Leisure Glen
![12 SAYVILLE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 828574 • BERKSHIRE HATHAWAY, Carole A. Dantuo...
The Greens at Half Hollow
![1069 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,140 sq ft
|Condo
1069 SAVOY DR, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 844110 • Douglas Elliman Real Estate, Cynthia...
Village Estates
![26 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701]()
2 beds
|2 baths
|1,243 sq ft
|Condo
26 SARAH CT, AMITYVILLE, NY, 11701
Community: Village Estates
MLS 866208 • EXIT Realty Premier, Nancy A. Fraser
Heritage Hills
![348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,428 sq ft
|Condo
348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 866206 • William Raveis-New York, LLC, Cynthi...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Jefferson Village
![6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 865906 • Keller Williams Realty Partner, Rose...
Glenwood Village
![1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901]()
2 beds
|1 baths
|753 sq ft
|Manufactured Home
1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
MLS 865948 • Joanne Kane Gigantiello, Joanne Giga...
Dutchgate
![1011 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580]()
MLS 864009 • North Star Homes Inc, Nimisha Baball
Fairfield at St. James
![1208 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,365 sq ft
|Condo
1208 FENWAY RD, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 856400 • Au Dela Real Estate LLC, Jessica L. ...
Leisure Glen
![6 BROOKVILLE CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 858951 • Signature Premier Properties, Elaine...
Frequently Asked Questions
In Cheshire, there is 1 small community with less than 500 homes.
The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.
No, there are no gated 55+ communities in Cheshire.
Want more information about active adult communities around Cheshire?
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